Butylated hydroxyanisole - CAS 25013-16-5
Molecular Formula:
C11H16O2
Molecular Weight:
180.247
COA:
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Description:
Butylated hydroxyanisole is used as an antioxidant and preservative in food, food packaging and animal feed.
Appearance:
White to Light Yellow Powder
Synonyms:
BHA
MSDS:
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InChIKey:
MRBKEAMVRSLQPH-UHFFFAOYSA-N
InChI:
InChI=1S/C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12/h5-7,12H,1-4H3
Canonical SMILES:
CC(C)(C)C1=C(C=CC(=C1)OC)O
1.Physiological Activities of Thiacremonone Produced in High Temperature and High Pressure Treated Garlic.
Woo KS1, Hwang IG2, Kim HY1, Lee SH3, Jeong HS3. Prev Nutr Food Sci. 2016 Mar;21(1):68-72. doi: 10.3746/pnf.2016.21.1.68. Epub 2016 Mar 31.
To examine the possibility of using thiacremonone isolated from high-temperature-high-pressure treated garlic, this study investigated the physiological activities properties. The IC50 values of hydroxyl, superoxide, hydrogen peroxide, and nitric oxide radical scavenging activities of thiacremonone were 92.50, 65.05, 12.60, and 81.53 μg/mL, respectively. On the other hand, the activities of vitamin C were 104.93, 99.43, 42.42, and 122.64 μg/mL, and the activities of butylated hydroxyanisole were 37.22, 68.45, 22.47, and 40.54 μg/mL, respectively. The IC50 value of ACE inhibition activities of thiacremonone and captoprill were 0.265 and 0.036 μg/mL, respectively. The IC50 value of xanthine oxidase inhibition activities of thiacremonone and allopurinol were 39.430 and 9.346 μg/mL, respectively. The IC50 value of tyrosinase inhibition activities of thiacremonone and kojic acid were 101.931 and 65.648 μg/mL, respectively.
2.Artifacts Generated During Azoalkane Peroxy Radical Oxidative Stress Testing of Pharmaceuticals Containing Primary and Secondary Amines.
Nefliu M1, Zelesky T2, Jansen P3, Sluggett GW2, Foti C2, Baertschi SW3,4, Harmon PA1. J Pharm Sci. 2015 Dec;104(12):4287-98. doi: 10.1002/jps.24667. Epub 2015 Nov 13.
We report artifactual degradation of pharmaceutical compounds containing primary and secondary amines during peroxy radical-mediated oxidative stress carried out using azoalkane initiators. Two degradation products were detected when model drug compounds dissolved in methanol/water were heated to 40°C with radical initiators such as 2,2'-azobis(2-methylpropionitrile) (AIBN). The primary artifact was identified as an α-aminonitrile generated from the reaction of the amine group of the model drug with formaldehyde and hydrogen cyanide, generated as byproducts of the stress reaction. A minor artifact was generated from the reaction between the amine group and isocyanic acid, also a byproduct of the stress reaction. We report the effects of pH, initiator/drug molar ratio, and type of azoalkane initiator on the formation of these artifacts. Mass spectrometry and nuclear magnetic resonance were used for structure elucidation, whereas mechanistic studies, including stable isotope labeling experiments, cyanide analysis, and experiments exploring the effects of butylated hydroxyanisole addition, were employed to support the degradation pathways.
3.Butylated Hydroxyanisole Potently Inhibits Rat and Human 11β-Hydroxysteroid Dehydrogenase Type 2.
Li L1, Wu Y, Wu X, Wang H, Bai Y, Wang X, Akingbemi BT, Huang P, Ge RS. Pharmacology. 2016;97(1-2):10-7. doi: 10.1159/000441034. Epub 2015 Nov 14.
Butylated hydroxyanisole (BHA) is a widely used antioxidant for food preservation. 11β-hydroxysteroid dehydrogenases, isoforms 1 (HSD11B1) and 2 (HSD11B2) have been demonstrated to be the regulators of the local level of active glucocorticoid, which has a broad range of physiological actions. In this study, the potency of BHA was tested for the inhibition of HSD11B1 and HSD11B2 in rat and human tissues. BHA showed potent inhibition of HSD11B2 with the half maximal inhibitory concentration calculated at 13.99 and 69.25 µmol/l for the rat and human, respectively. Results showed that BHA competitively inhibited HSD11B2 when a steroid substrate was used. However, it served as a mixed inhibition factor when the cofactor NAD+ was used. In contrast, the potency of BHA to inhibit both rat and human HSD11B1 was diminished, with the concentration of 100 μmol/l causing no inhibitory effect on the isoform. In conclusion, we observed that BHA is a selective inhibitor of HSD11B2, implying that this agent may cause excessive glucocorticoid action in local tissues such as kidney and placentas.
4.Individual and combined in vitro (anti)androgenic effects of certain food additives and cosmetic preservatives.
Pop A1, Drugan T2, Gutleb AC3, Lupu D4, Cherfan J5, Loghin F6, Kiss B7. Toxicol In Vitro. 2016 Apr;32:269-77. doi: 10.1016/j.tiv.2016.01.012. Epub 2016 Jan 23.
The individual and combined (binary mixtures) (anti)androgenic effect of butylparaben (BuPB), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and propyl gallate (PG) was evaluated using the MDA-kb2 cell line. Exposing these cells to AR agonists results in the expression of the reporter gene (encoding for luciferase) and luminescence can be measured in order to monitor the activity of the reporter protein. In case of the evaluation of the anti-androgenic effect, the individual test compounds or binary mixtures were tested in the presence of a fixed concentration of a strong AR agonist (1000pM 5-alpha-dihydrotestosterone; DHT). Cell viability was assessed using a resazurin based assay. For PG, this is the first report in the literature concerning its (anti)androgenic activity. In case of both individual and mixture testing none of the compounds or binary combinations showed androgenic activity. When tested in the presence of DHT, BuPB, BHA and BHT proved to be weak anti-androgens and this was confirmed during the evaluation of binary mixtures (BuPB+BHA, BuPB+BHT and BHA+BHT).
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CAS 25013-16-5 Butylated hydroxyanisole

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